EP0632327B1 - Composition pour photoréserve - Google Patents

Composition pour photoréserve Download PDF

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Publication number
EP0632327B1
EP0632327B1 EP94108468A EP94108468A EP0632327B1 EP 0632327 B1 EP0632327 B1 EP 0632327B1 EP 94108468 A EP94108468 A EP 94108468A EP 94108468 A EP94108468 A EP 94108468A EP 0632327 B1 EP0632327 B1 EP 0632327B1
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EP
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Prior art keywords
polyvinylphenol
photoresist composition
partially
composition according
pattern
Prior art date
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Expired - Lifetime
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EP94108468A
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German (de)
English (en)
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EP0632327A1 (fr
Inventor
Yuko Nakano
Naoki Takeyama
Yuji Ueda
Takehiro Kusumoto
Hiromi Oka
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/12—Nitrogen compound containing
    • Y10S430/121—Nitrogen in heterocyclic ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/122—Sulfur compound containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/124—Carbonyl compound containing
    • Y10S430/125—Carbonyl in heterocyclic compound

Definitions

  • the present invention relates to a resist compositions particularly suitable for use in lithography using far ultraviolet rays including excimer laser.
  • polyvinylphenol As an alkali-soluble resin in such chemical amplification type resists, polyvinylphenol has hitherto been widely used.
  • the solubility of the polyvinylphenol in an alkaline developer is too high, and due to the high solubility, a photoresist exhibiting sufficient sensitivity and sufficient resolution cannot be obtained.
  • the present invention provides a chemical amplification type negative photoresist composition which comprises (A) an alkali soluble resin containing at least one resin selected from the group consisting of a partially alkyletherified polyvinylphenol (herein after denoted to as A1) and a partially alkyletherified hydrogenated polyvinylphenol (herein after denoted to as A2); (B) a photo-induced acid precursor containing at least a kind of sulfonic acid esters of N-hydroxyimide compounds; and (C) a cross-linking agent.
  • A1 partially alkyletherified polyvinylphenol
  • A2 partially alkyletherified hydrogenated polyvinylphenol
  • A2 partially alkyletherified hydrogenated polyvinylphenol
  • B a photo-induced acid precursor containing at least a kind of sulfonic acid esters of N-hydroxyimide compounds
  • C a cross-linking agent
  • Examples of the sulfonic acid esters of N-hydroxyimide compounds include an ester represented by the following formula (I): wherein R 1 is an optionally substituted arylene, alkylene or alkenylene group and R 2 is an optionally substituted alkyl or aryl group.
  • Examples of the arylene group denoted by R 1 in the formula (I) include monocyclic and bicyclic arylene groups, among them phenylene or naphthylene are preferred. As preferred substituents on the arylene group, halogen atoms, nitro groups or acetylamino groups can be referred to.
  • alkylene groups denoted by R 1 in the formula (I) include straight chain and branched chain alkylene groups, among which those having 1 to 6 carbon atoms are preferable and particularly preferable are ethylene or propylene.
  • halogen atoms, lower alkoxy groups or monocyclic aryl groups can be referred to.
  • alkenylene groups denoted by R 1 in the formula (I) include those having 2 to 6 carbon atoms, among which vinylidene is preferable.
  • alkenylene group monocyclic aryl groups can be referred to.
  • alkyl groups denoted by R 2 in the formula (I) include straight chain and branched chain alkyl groups, among which those having 1 to 8 carbon atoms are preferable.
  • R 2 in the formula (I) examples include straight chain and branched chain alkyl groups, among which those having 1 to 8 carbon atoms are preferable.
  • lower alkoxy groups can be referred to.
  • Examples of the aryl groups denoted by R 2 in the formula (I) include monocyclic and bicyclic aryl groups, among which monocyclic aryl groups are preferable.
  • R 2 is a substituted alkyl or aryl group, it is preferable that its substituent is not a fluorine atom.
  • esters represented by the formula (I) can be produced, for example, by reacting a cyclic N-hydroxyimide compound represented by the following formula (III): wherein R 1 is as defined above, and which can be produced according to a method described in, for example, G. F. Jaubert, Ber., 28 , 360 (1985), D. E. Ames et al., J. Chem. Soc., 3518 (1955) or M. A. Stolberg et al., J. Amer. Chem.
  • esters represented by the formula (I) can be used either independently or in the form of a mixture of two or more.
  • Resin A1 is preferably a partially alkyletherified poly(p-vinylphenol) which alkyletherification ratio is from 10 to 35 mole%.
  • the resin A2 preferable is that having an alkyletherification ratio being from 5 to 30 mole%.
  • the mixing ratio of resin A1 and A2 is determined according to the situation where they are used.
  • An alkali-soluble resin other than the resin A1 and A2 can be contained in the above-mentioned resin (A).
  • the alkali-soluble resin other than the resin A1 and A2 include vinylphenol resins, isopropenylphenol resins, copolymers of vinylphenol and styrene (preferable molar ratio of the vinylphenol in the copolymer is 50% or more.), copolymers of isopropenylphenol and styrene (preferable molar ratio of the isopropenylphenol in the copolymer is 50% or more.), or hydrogenated polyvinylphenol.
  • the mixing ratio of the alkali-soluble resin other than A1 and A2 to the resin A1 and A2 can be determined according to the situation where they are used, as long as the object of the present invention is attained.
  • alkylether examples include straight chain and branched chain alkylethers, among which those having 1 to 4 carbon atoms are preferable, and particularly preferable is methylether or ethylether.
  • a preferable alkyletherification ratio of the resin A1 is from 15 to 22 mole% and that of the resin A2 is from 8 to 20 mole%.
  • the resin A1 can be produced by reacting a polyvinylphenol with an alkyl halide according to a method described in, for example, G. N. Vyas et al., Org. Syntheses Coll. Vol. IV, 836 (1963), etc.
  • the resin A2 can be produced by reacting a hydrogenated polyvinylphenol with an alkyl halide according to a method described in, for example, above-mentioned G. N. Vyas et al., etc.
  • the hydrogenated polyvinylphenol can be produced by a hydrogenation of a polyvinylphenol according to a usual method.
  • the alkali-soluble resins A1 and A2 usually have a weight average molecular weight of from 1,000 to 10,000 measured by GPC calculated as polystyrene, preferably from 1,500 to 8,000 and particularly preferably from 2,000 to 5,000.
  • cross-linking agent examples include the compounds having methylol groups or methylol-ether groups described in, for example, Japanese Patent Application No. 92-15009. As the preferable examples, the following can be referred to:
  • cross-linking agents having methylol groups or methylol-ether groups can be used either independently or in the form of a mixture of two or more.
  • the mixing ratio of the ingredients is preferably as follows: alkali-soluble resin from 50 to 95 % by weight, cross-linking agent from 1 to 30 % by weight, photo induced acid precursor from 1 to 20 % by weight.
  • additives conventionally used in this field of art such as sensitizers, dyes, adhesion or improvers may be added, if desired.
  • a photoresist solution is usually prepared by mixing the above-mentioned negative photoresist composition into a solvent so that the concentration of the composition in the total mixture comes to 10 to 50 % by weight.
  • the solvents usable for this purpose include ethyl cellosolve acetate, methyl cellosolve acetate, ethyl cellosolve, methyl cellosolve, propyleneglycol monomethylether acetate, propyleneglycol monoethylether acetate, propyleneglycol monomethylether, propyleneglycol monoethylether, diethyleneglycol dimethylether, ethyl lactate, butyl acetate, ethyl pyruvate, 2-heptanone, cyclohexanone, methyl-isobutyl ketone, or xylene.
  • solvents can be used either independently or in combination of two or more.
  • the positive photoresist compositions and the negative photoresist compositions of the present invention are excellent in various properties such as heat resistance, film thickness retention, coatability, profile and the like. They further exhibit high sensitivity and high resolution when far ultraviolet rays including excimer lasers are used as the light source. They also have the advantage that minute residue (scam) is hardly caused during the developing process, particularly when the alkali-soluble resin is A2. Accordingly, in the lithography using the above-mentioned light source, the resolution and the contrast can be remarkably improved and highly precise fine photoresist pattern can be formed.
  • Referential Example 1 was repeated except 3.84 g, 3.90 g or 2.96 g of ethyl iodide was used instead of 3.38 g of ethyl iodide used in Referential Example 1 to obtain partially ethyletherified polyvinylphenol having an ethyletherification ratio of 20.3 mole%, 21.8 mole% or 16.7 mole%, respectively.
  • a silicon wafer washed in a conventional manner was coated with the resist solution thus prepared by mean of a spinner so as to give a coating thickness of 0.7 ⁇ m. Then the silicone wafer was prebaked on a hotplate at 100°C for 1 minute. The prebaked coating film was exposed to light through a patterned chrome mask with KrF Excimer Laser Stepper (NSR-1755, EX8A, NA 0.45, manufactured by Nicon Co.) using 248 nm ultraviolet ray. After the exposure, the wafer was heated on a hot plate at 100°C for 1 minute to cause cross-linking reaction at the exposed part.
  • the wafer was developed with a 2.38 % aqueous solution of tetramethylammonium hydroxide to form a negative pattern. Then, the pattern thus formed was observed by means of electron microscope. The observation revealed that 0.25 ⁇ m of the fine line-and-space pattern could be resolved at the exposure dose of 42mJ/cm 2 (248 nm, effective sensitivity) with a good profile and no scam was observed at the unexposed part.
  • Example 1 was repeated except that partially ethyletherified polyvinylphenol obtained in Referential Example 2 was used instead of the partially ethyletherified polyvinylphenol obtained in Referential Example 1 to obtain a negative pattern.
  • the pattern thus formed was observed by means of electron microscope and it was revealed that 0.25 ⁇ m of the line-and-space pattern could be resolved at the exposure dose of 25mJ/cm 2 (248 nm).
  • Example 1 was repeated except that partially ethyletherified polyvinylphenol obtained in Referential Example 3 was used instead of the partially ethyletherified polyvinylphenol obtained in Referential Example 1 to obtain a negative pattern.
  • the pattern thus formed was observed by means of electron microscope and it was revealed that 0.25 ⁇ m of the line-and-space pattern could be resolved at the exposure dose of 20mJ/cm 2 (248 nm).
  • Example 1 was repeated except that partially ethyletherified polyvinylphenol obtained in Referential Example 4 was used instead of the partially ethyletherified polyvinylphenol obtained in Referential Example 1 to obtain a negative pattern.
  • the pattern thus formed was observed by means of electron microscope and it was revealed that 0.25 ⁇ m of the line-and-space pattern could be resolved at the exposure dose of 29mJ/cm 2 (248 nm).
  • Example 1 was repeated except that, as the alkali-soluble resin, the mixture of 8.1 parts of partially ethyletherified polyvinylphenol obtained in Referential Example 2 and 5.4 parts of copolymer of vinylphenol and styrene (LYNCUR CST-70; weight average molecular weight 1720; molar ratio of vinylphenol to styrene is 70 : 30 ; manufactured by Maruzen Petrochemical Co.) was used instead of the partially ethyletherified polyvinylphenol obtained in Referential Example 1 to obtain a negative pattern. The pattern thus formed was observed by means of electron microscope and it was revealed that 0.25 ⁇ m of the line-and-space pattern could be resolved at the exposure dose of 27mJ/cm 2 (248 nm).
  • LYNCUR CST-70 copolymer of vinylphenol and styrene
  • a silicon wafer washed in the conventional manner was coated with the resist solution by means of a spinner so as to give a coating thickness of 0.7 ⁇ m. Then the silicone wafer was prebaked on a hotplate at 100°C for 1 minute. The prebaked coating film was exposed to light through a patterned chrome mask with KrF Excimer Laser Stepper (NSR-1755, EX8A, NA 0.45, manufactured by Nicon Co.) using 248 nm ultraviolet ray. After the exposure, the wafer was heated on a hot plate at 105°C for 1 minute to cause cross-linking reaction at the exposed part. Thereafter, the wafer was developed with a 2.0% aqueous solution of tetramethylammonium hydroxide to form a negative pattern. Then, the pattern thus formed was observed by means of electron microscope and it was revealed that only 0.35 ⁇ m of the line-and-space pattern could be resolved at the exposure dose of 50mJ/cm 2 (248 nm).
  • the acetone layer was separated and poured into 2000 ml of ion exchanged water to cause deposition.
  • the deposited product was collected by filtration, and dryed to obtain partially ethyletherified hydrogenated polyvinylphenol having the ethyletherification ratio of 15 mole%.
  • the silicone wafer was prebaked on a hot plate at 100°C for 1 minute.
  • the wafer was heated on a hot plate at 100°C for 1 minute to cause cross-linking reaction at the exposed part.
  • the wafer was developed with a 2.38% aqueous solution of tetramethylammonium hydroxide to form a negative pattern.
  • the pattern thus formed was observed by means of electron microscope. The observation revealed that 0.25 ⁇ m of the fine line-and-space pattern could be resolved at the exposure dose of 25 mJ/cm 2 (248 nm) with a good profile and no scam was observed at the unexposed part.

Claims (5)

  1. Composition de photorésist négatif qui comprend:
    (A) une résine soluble dans les bases contenant au moins une résine choisie dans le groupe formé par un polyvinylphénol partiellement alkyléthérifié et un polyvinylphénol hydrogéné partiellement alkyléthérifié;
    (B) un précurseur acide photo-induit contenant au moins un type d'esters d'acide sulfonique de composés N-hydroxyimide; et
    (C) un agent de réticulation.
  2. Composition de photorésist selon la revendication 1, dans laquelle la résine soluble dans les bases est un poly(p-vinylphénol) partiellement alkyléthérifié ayant un taux d'alkyléthérification de 10 à 35%.
  3. Composition de photorésist selon la revendication 1, dans laquelle la résine soluble dans les bases est un polyvinylphénol hydrogéné partiellement alkyléthérifié ayant un taux d'alkyléthérification de 5 à 30%.
  4. Composition de photorésist selon l'une quelconque des revendications 1 à 3, dans laquelle l'ester d'acide sulfonique du composé N-hydroxyimide est un composé représenté par la formule suivante (I):
    Figure 00230001
    dans laquelle R1 est un groupe arylène éventuellement substitué, alkylène ou alcénylène et R2 est un groupe alkyle ou aryle éventuellement substitué.
  5. Composition de photorésist selon la revendication 4, dans laquelle R2 est un groupe alkyle ou aryle éventuellement substitué à condition que, quand R2 est un groupe alkyle ou aryle substitué, son substituant ne soit pas un atome de fluor.
EP94108468A 1993-06-02 1994-06-01 Composition pour photoréserve Expired - Lifetime EP0632327B1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP13198693 1993-06-02
JP131986/93 1993-06-02
JP13198693 1993-06-02
JP3366094 1994-03-03
JP33660/94 1994-03-03
JP3366094 1994-03-03

Publications (2)

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EP0632327A1 EP0632327A1 (fr) 1995-01-04
EP0632327B1 true EP0632327B1 (fr) 2000-09-06

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US (1) US5585218A (fr)
EP (1) EP0632327B1 (fr)
KR (1) KR100354680B1 (fr)
CA (1) CA2124667A1 (fr)
DE (1) DE69425786T2 (fr)
TW (1) TW288112B (fr)

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KR100907820B1 (ko) * 2001-12-27 2009-07-14 니폰 제온 가부시키가이샤 방사선-감수성 수지 조성물 및 패턴 형성 방법
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JP4724465B2 (ja) * 2005-05-23 2011-07-13 富士フイルム株式会社 感光性組成物及び該感光性組成物を用いたパターン形成方法
JP5703197B2 (ja) 2011-01-18 2015-04-15 富士フイルム株式会社 化学増幅型レジスト組成物、それを用いたレジスト膜、レジスト塗布マスクブランクス、レジストパターン形成方法、及び、フォトマスク、並びに、高分子化合物
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JP2847413B2 (ja) * 1990-01-30 1999-01-20 和光純薬工業株式会社 レジスト材料
JP2970879B2 (ja) * 1990-01-30 1999-11-02 和光純薬工業株式会社 化学増幅型レジスト材料
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JP2583651B2 (ja) * 1990-09-28 1997-02-19 東京応化工業株式会社 ネガ型感放射線レジスト組成物
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TW207009B (fr) * 1991-01-31 1993-06-01 Sumitomo Chemical Co
JPH04291261A (ja) * 1991-03-19 1992-10-15 Nippon Zeon Co Ltd レジスト組成物
DE4112972A1 (de) * 1991-04-20 1992-10-22 Hoechst Ag Negativ arbeitendes strahlungsempfindliches gemisch und damit hergestelltes strahlungsempfindliches aufzeichnungsmaterial
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US5292614A (en) * 1991-08-02 1994-03-08 Mitsubishi Kasei Corporation Negative photosensitive composition and method for forming a resist pattern
US5286600A (en) * 1991-08-27 1994-02-15 Mitsubishi Kasei Corporation Negative photosensitive composition and method for forming a resist pattern by means thereof
JP2655384B2 (ja) * 1991-11-08 1997-09-17 富士写真フイルム株式会社 ポジ型レジスト組成物
JPH05181277A (ja) * 1991-11-11 1993-07-23 Mitsubishi Kasei Corp ネガ型感光性組成物
US5296332A (en) * 1991-11-22 1994-03-22 International Business Machines Corporation Crosslinkable aqueous developable photoresist compositions and method for use thereof

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Publication number Publication date
CA2124667A1 (fr) 1994-12-03
EP0632327A1 (fr) 1995-01-04
KR100354680B1 (ko) 2003-03-19
TW288112B (fr) 1996-10-11
DE69425786D1 (de) 2000-10-12
US5585218A (en) 1996-12-17
KR950001415A (ko) 1995-01-03
DE69425786T2 (de) 2001-01-25

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